When Mike Ditka, the coach of the New Orleans Saints, returns to his old Chicago haunts, he checks into the dignified Tremont, staying in a suite conveniently adjacent to his Iron Mike's Grille on East Chestnut Street. Built in 1923, this newly renovated, European-style "boutique" hotel, with its classic stone facade, is neither large nor impersonal. The intimate scale of the hotel ensures that the staff can do most anything to cater to their guests.

From the VCRs and minibars to the marble bathrooms and the traditional decor punctuated with antiques, the Tremont's rooms offer the luxury of unexpected details and the grandeur of space. There's also a fitness center to help you work off any jet lag, whether you're a football coach or a stock analyst.

Next door to the hotel is the Tremont House, which offers longer-term rooms with kitchens and a massage room (with a full-time masseur). "What separates our hotel is the service," says Wolf. "Since we're smaller, we have much more ability to go that extra mile and exceed the guest's expectations."

Just a touchdown pass from Michigan Avenue and the shopping along the famed "Magnificent Mile," the Tremont Hotel lobby leads directly into Iron Mike's Grille. Iron Mike's isn't some sports bar with 30 TV screens, serving five different burgers and 10 sandwiches named after ballplayers. Rather, it is a casual restaurant whose dishes are the personal creations of renowned Chicago restaurateur Joe Carlucci. You'll need room to tackle a meal worthy of inclusion in The Guiness Book of World Records--the 20-ounce pork chop. Or you might go for other feasts, such as the Kick-Ass Paddle Steak or the Training Table Pot Roast. Whatever you're eating, you'll be in good company, as murals of such Chicago sports legends as George Halas, Dick Butkus, Bobby Hull and Stan Mikita vie for your attention. And business travelers who might need a little more room can take advantage of Iron Mike's 5,000 square feet of meeting and banquet rooms.

The Tremont and Iron Mike's are at once cozy stops and looking-glasses, peering out on a universe of choices. Sparkling Lake Michigan laps at Lake Shore Drive, stirring clean breezes on the town's northern shore just a few blocks away. Within a half-mile walk there's the John Hancock Building, the Water Tower (one of the few edifices that survived the Chicago fire of 1871), the Tribune Tower, the Wrigley Building, the Lincoln Park Zoo and the Museum of Contemporary Art.

Stroll along Michigan Avenue, and you'll see ample reminders of Michael Jordan, with many shops displaying Bulls literature and red-and-black paraphernalia. The Windy City is reputed to be "Cubs Town," but even though the ballclub reached the playoffs last fall, one would have an easier time finding a monument to Carl Sandburg than to Ryne Sandberg.

After weaving in and out of Michigan Avenue's foot traffic, you may well be ready for a glass of B&B and a cigar nightcap. Kick your feet up, watch the cigar smoke drift away and think of the next day's serendipitous journey around the city.--Kenneth Shouler

Kenneth Shouler is a freelance writer based in White Plains, New York.